CN119684065A - Bispyridine bisamide organic ligand for regulating soil urease activity and inhibiting nitrification and preparation method thereof - Google Patents
Bispyridine bisamide organic ligand for regulating soil urease activity and inhibiting nitrification and preparation method thereof Download PDFInfo
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Abstract
The invention provides a bipyridine bisamide organic ligand for regulating the activity of soil urease and inhibiting nitrification and a preparation method thereof, belonging to the technical field of coordination complexes. According to the invention, the dipyridine bisamide organic ligand is obtained by using the chlorinated 4,4' -stilbene dicarboxylic acid and the halogen-containing pyridine compound and introducing the sulfhydryl-containing sulfur quantum dot, so that the soil nitrate reductase can be effectively reduced while the soil urease activity is improved.
Description
Technical Field
The invention belongs to the technical field of coordination complexes, and particularly relates to a bipyridine bisamide organic ligand for regulating soil urease activity and inhibiting nitrification and a preparation method thereof.
Background
Coordination polymers (which may be referred to as complexes or complexes) are inorganic-organic hybrid materials obtained by self-assembling transition metals, such as Co, zn, cu, etc., with organic ligands. The complex combines the advantages of inorganic materials such as high fire resistance, light weight and environmental protection, and has the characteristics of organic materials such as porosity and good designability due to the special construction mode. Ligands (abbreviated as ligands) are classified into monodentate ligands having one coordinating atom and capable of directly coordinating with a central atom, and multidentate ligands having two or more coordinating atoms and capable of forming various coordination modes with the central atom, such as chelate coordination, depending on the number of coordinating atoms.
The invention discloses a transition metal complex based on semi-rigid bipyridine bisamide organic ligand and terephthalic acid, and a synthesis method and application thereof, wherein the semi-rigid bipyridine bisamide ligand N, N' -bis (3-pyridine amide) -1, 2-cyclohexane is adopted as a neutral organic amine ligand, not only is pyridine nitrogen atom coordinated with metal ions, but also amide oxygen atom is a potential coordination point, and the introduction of amide groups increases the hydrophilicity of the ligand, accelerates the crystallization process during the synthesis of the transition metal complex, shortens the synthesis period, shortens the constant temperature time and reduces the power consumption. However, the technology of the patent still does not solve the problem that when the bipyridine bisamide organic ligand is applied to soil fertilizers, the activity of soil urease cannot be effectively regulated and nitrification can be inhibited, so that the use of the bipyridine bisamide organic ligand is limited.
Therefore, there is a need for a bipyridine bisamide organic ligand that can effectively reduce soil nitrate reductase while improving soil urease activity by functionalizing the raw material components and introducing the modifying components.
Disclosure of Invention
The invention aims to provide a bipyridine bisamide organic ligand for regulating the activity of soil urease and inhibiting nitrification and a preparation method thereof, wherein chlorinated 4,4' -stilbene dicarboxylic acid and halogen-containing pyridine compounds are used, and mercapto sulfur quantum dots are introduced to obtain the bipyridine bisamide organic ligand, so that the activity of the soil urease is improved, and meanwhile, the nitrate reductase of the soil is effectively reduced.
In order to achieve the above object, the present invention provides the following technical solutions:
the first aspect of the invention provides a method for preparing a bipyridine bisamide organic ligand for regulating the activity of soil urease and inhibiting nitrification, which comprises the following steps:
step S1, adding 20-25 parts of 4,4 '-stilbene dicarboxylic acid and 12-15 parts of N-chlorosuccinimide into 40-50 parts of dichloromethane, stirring for 10-20 min, adding 2-4 parts of trifluoroacetic acid, stirring and reacting for 12-24 h to obtain a reaction mixture, pouring the reaction mixture into ice water, extracting with an organic solvent, drying, concentrating, and recrystallizing to obtain chlorinated 4,4' -stilbene dicarboxylic acid;
And S2, adding 6-8 parts of the chlorinated 4,4' -stilbenedicarboxylic acid, 4-6 parts of pyridine compound and 0.2-0.5 part of quantum dot material into 60-70 parts of pyridine, stirring for 30-60 min, adding 14-16 parts of triphenyl phosphite, heating to 110-120 ℃, refluxing for 10-12 h, cooling, standing, suction filtering, collecting solids, washing with absolute ethyl alcohol, and drying to obtain the bipyridine bisamide organic ligand for regulating the urease activity of soil and inhibiting nitrification.
The chloridized 4,4' -stilbene dicarboxylic acid can provide chlorine element for microorganisms, promote the growth and metabolism of the microorganisms, indirectly improve the urease activity by means of the improvement of the microbial activity, and meanwhile, the chlorine element can form soluble complex with metal ions in soil, so that the bioavailability of the metal ions is improved, and the metal ions can be ensured to be used as important auxiliary factors of the urease activity.
As a preferred embodiment, the organic solvent in the step S1 is diethyl ether or ethyl acetate.
As a preferred embodiment, the pyridine compound in the step S2 is a halogen-containing pyridine compound.
As a preferred embodiment, the halogen-containing pyridines are 2-fluoro-3-amino-4-methylpyridine and 2-bromo-3-amino-4-methylpyridine.
As a preferable mode, the mass ratio of the 2-fluoro-3-amino-4-methylpyridine to the 2-bromo-3-amino-4-methylpyridine is (1-2): 1.
The halogen in the pyridine compound can be combined with key amino acid residues of the nitrifying enzyme to interfere an active site of the enzyme, so that the activity of the nitrifying enzyme is reduced, and simultaneously, the halogen can also interfere the cell membrane structure and function of nitrifying bacteria, inhibit the growth and metabolism of the nitrifying bacteria, and comprehensively affect the activity of the nitrifying bacteria to inhibit the nitrifying action.
As a preferred scheme, the quantum dot material in step S2 is a sulfur quantum dot containing mercapto group.
According to the preparation method, 5-10 parts of sulfur quantum dots are dispersed in 40-50 parts of deionized water to obtain sulfur quantum dot mixed liquid, then the sulfur quantum dot mixed liquid is subjected to plasma treatment, 1-3 parts of thioglycollic acid and 0.2-0.5 part of 1-hydroxybenzotriazole are added into the sulfur quantum dot mixed liquid after the plasma treatment is completed, stirring is carried out for 2-4 hours, and after the reaction is completed, centrifugation, washing and drying are carried out to obtain the sulfur quantum dot containing mercapto.
According to the preparation method, 4-6 parts of sodium hydroxide and 3-5 parts of polyethylene glycol are added into 40-50 parts of deionized water, 1-2 parts of sulfur powder is added after uniform stirring, orange red solution is obtained after stirring for 2-4 hours at 70-75 ℃, air is introduced into the orange red solution by using a peristaltic pump and continuously reacts for 20-24 hours, 10-12 parts of 35% hydrogen peroxide solution is dropwise added after the reaction is finished for reacting for 40-60 minutes, the reaction is completed, the temperature is cooled to room temperature to obtain pale yellow solution, and the pale yellow solution is dialyzed, steamed and freeze-dried to obtain the sulfur quantum dot.
As a preferred embodiment, the sulfur powder has an average particle size of 0.5. Mu.m.
The charge on the surface of the sulfhydryl-containing sulfur quantum dot can form a complex with positively charged metal ions in soil through electrostatic attraction, and the utilization rate of the metal ions by the soil urease is improved through the complex form, so that the activity of the soil urease is improved.
In a second aspect, the invention provides a bipyridine bisamide organic ligand which is prepared by the preparation method according to the first aspect and is used for regulating the activity of soil urease and inhibiting nitrification.
Compared with the prior art, the invention has the advantages that:
1. The sulfhydryl of the sulfur quantum dot of the invention forms a covalent bond with the key amino acid residue of the nitrifying enzyme to interfere the active site of the nitrifying enzyme, and the halogen in the pyridine compound can be combined with the active site of the nitrifying enzyme to further reduce the activity of the nitrifying enzyme, thereby inhibiting the nitrification.
2. The chloridized 4,4' -stilbene dicarboxylic acid can provide chlorine elements for microorganisms, promote the growth and metabolism of the microorganisms, indirectly improve the urease activity by means of the improvement of the microbial activity, and meanwhile, the chlorine elements can form soluble complexes with metal ions in soil, so that the bioavailability of the metal ions is improved, and the metal ions can be ensured to be used as important auxiliary factors of the urease activity.
3. The halogen in the pyridine compound can be combined with key amino acid residues of the nitrifying enzyme to interfere active sites of the enzyme, so that the activity of the nitrifying enzyme is reduced, and simultaneously, the halogen can also interfere the cell membrane structure and function of nitrifying bacteria, inhibit the growth and metabolism of the nitrifying bacteria, and comprehensively affect the activity of the nitrifying bacteria to inhibit the nitrifying action.
4. The charge on the surface of the sulfhydryl-containing sulfur quantum dot can form a complex with positively charged metal ions in soil through electrostatic attraction, and the utilization rate of the metal ions by the soil urease is improved through the complex form, so that the activity of the soil urease is improved.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The partial sources of the examples and comparative examples are as follows:
4,4' -stilbenedicarboxylic acid, CAS number 100-31-2, available from Shanghai Ala Biochemical technologies Co., ltd;
3-amino-4-methylpyridine, CAS number 3430-27-1, available from Shanghai Ala Biotechnology Co., ltd;
pyridine, CAS number 110-86-1, available from national pharmaceutical group chemical Co., ltd;
Triphenyl phosphite, CAS number 101-02-0, available from the chemical industry company, inc. In the south through ken;
N-chlorosuccinimide, CAS number 128-09-6, available from Shanghai Ala Biochemical technologies Co., ltd;
Dichloromethane, CAS No. 75-09-2, available from national pharmaceutical group chemical company, inc;
trifluoroacetic acid, CAS number 76-05-1, available from Guogou chemical Co., ltd;
Absolute ethyl alcohol, CAS number 64-17-5, available from Guogou chemical reagent Co., ltd;
ethyl acetate, CAS No. 141-78-6, available from national pharmaceutical group chemical company, inc;
Diethyl ether, CAS number 60-29-7, available from Guogou Chemicals Co., ltd;
2-fluoro-3-amino-4-methylpyridine, CAS number 173435-32-0, available from Shanghai aladine Biochemical technologies Co., ltd;
2-bromo-3-amino-4-methylpyridine, CAS number 126325-50-6, available from Shanghai Ala Di Biochemical technologies Co., ltd;
polyethylene glycol, cat No. 202398-250G, available from sigma-aldrich company;
Sulfur powder I, having an average particle size of 0.5 μm, available from An Naiji (Shanghai) pharmaceutical chemical company, inc;
sulfur powder II, having an average particle size of 45 μm, available from sigma-aldrich company;
Hydrogen peroxide solution, product number H433859-250ml, mass concentration 35%, purchased from Shanghai aladine Biochemical technologies Co., ltd;
thioglycollic acid, CAS number 68-11-1, available from Tokyo chemical Co., ltd;
1-hydroxybenzotriazole, CAS number 2592-95-2, available from Shanghai Annaiji chemical company.
Example 1
The embodiment provides a preparation method of bipyridine bisamide organic ligand for regulating soil urease activity and inhibiting nitrification, which comprises the following steps:
Adding 6 parts of sodium hydroxide and 5 parts of polyethylene glycol into 50 parts of deionized water, stirring uniformly, adding 2 parts of sulfur powder (sulfur powder I, average particle size of 0.5 mu m), stirring for 2 hours at 75 ℃ to obtain orange red solution, introducing air into the orange red solution by using a peristaltic pump, continuing to react for 24 hours, dropwise adding 12 parts of 35% hydrogen peroxide solution by mass after the reaction is finished, reacting for 60 minutes, cooling to room temperature after the reaction is finished to obtain pale yellow solution, dialyzing, steaming, and freeze-drying to obtain the sulfur quantum dots. (2) According to parts by weight, dispersing 10 parts of sulfur quantum dots in 50 parts of deionized water to obtain sulfur quantum dot mixed solution, then carrying out plasma treatment on the sulfur quantum dot mixed solution, adding 3 parts of thioglycollic acid and 0.5 part of 1-hydroxybenzotriazole into the sulfur quantum dot mixed solution after the plasma treatment is finished, stirring and reacting for 4 hours, centrifuging after the reaction is finished, washing and drying to obtain the sulfur quantum dot containing sulfhydryl.
Step S1, adding 25 parts of 4,4 '-stilbene dicarboxylic acid and 15 parts of N-chlorosuccinimide into 50 parts of dichloromethane, stirring for 20min, adding 4 parts of trifluoroacetic acid, stirring and reacting for 24h to obtain a reaction mixture, pouring the reaction mixture into ice water, extracting with ethyl acetate, drying, concentrating, and recrystallizing to obtain chlorinated 4,4' -stilbene dicarboxylic acid;
And S2, adding 8 parts of chlorinated 4,4' -stilbenedicarboxylic acid, 4 parts of 2-fluoro-3-amino-4-methylpyridine, 2 parts of 2-bromo-3-amino-4-methylpyridine and 0.5 part of sulfur containing sulfydryl quantum dot into 70 parts of pyridine, stirring for 60min, then adding 16 parts of triphenyl phosphite, heating to 120 ℃, refluxing for 10h, cooling, standing, suction filtering, collecting solid, washing with absolute ethyl alcohol, and drying to obtain the bipyridine bisamide organic ligand capable of regulating the urease activity of soil and inhibiting nitrification.
Example 2
The embodiment provides a preparation method of bipyridine bisamide organic ligand for regulating soil urease activity and inhibiting nitrification, which comprises the following steps:
Adding 4 parts of sodium hydroxide and 3 parts of polyethylene glycol into 40 parts of deionized water, stirring uniformly, adding 1 part of sulfur powder (sulfur powder I, average particle size of 0.5 mu m), stirring for 4 hours at 70 ℃ to obtain orange red solution, introducing air into the orange red solution by using a peristaltic pump, continuing to react for 20 hours, dropwise adding 10 parts of 35% hydrogen peroxide solution by mass after the reaction is finished, reacting for 40 minutes, cooling to room temperature after the reaction is finished to obtain pale yellow solution, dialyzing, steaming, and freeze-drying to obtain the sulfur quantum dots. (2) According to parts by weight, dispersing 5 parts of sulfur quantum dots in 40 parts of deionized water to obtain sulfur quantum dot mixed solution, then carrying out plasma treatment on the sulfur quantum dot mixed solution, adding 1 part of thioglycollic acid and 0.2 part of 1-hydroxybenzotriazole into the sulfur quantum dot mixed solution after the plasma treatment is finished, stirring and reacting for 2 hours, centrifuging after the reaction is finished, washing and drying to obtain the sulfur quantum dot containing sulfhydryl.
Step S1, adding 20 parts of 4,4 '-stilbene dicarboxylic acid and 12 parts of N-chlorosuccinimide into 40 parts of dichloromethane, stirring for 10min, adding 2 parts of trifluoroacetic acid, stirring and reacting for 12h to obtain a reaction mixture, pouring the reaction mixture into ice water, extracting with diethyl ether, drying, concentrating, and recrystallizing to obtain chlorinated 4,4' -stilbene dicarboxylic acid;
and S2, adding 6 parts of chlorinated 4,4' -stilbenedicarboxylic acid, 2 parts of 2-fluoro-3-amino-4-methylpyridine, 2 parts of 2-bromo-3-amino-4-methylpyridine and 0.2 part of sulfur containing sulfydryl quantum dots into 60 parts of pyridine, stirring for 30min, adding 14 parts of triphenyl phosphite, heating to 110 ℃, refluxing for 12h, cooling, standing, suction filtering, collecting solids, washing with absolute ethyl alcohol, and drying to obtain the bipyridine bisamide organic ligand capable of regulating the urease activity of soil and inhibiting nitrification.
Example 3
The embodiment provides a preparation method of bipyridine bisamide organic ligand for regulating soil urease activity and inhibiting nitrification, which comprises the following steps:
Adding 5 parts of sodium hydroxide and 4 parts of polyethylene glycol into 45 parts of deionized water, stirring uniformly, adding 2 parts of sulfur powder (sulfur powder I, average particle size of 0.5 mu m), stirring for 3 hours at 72 ℃ to obtain orange red solution, introducing air into the orange red solution by using a peristaltic pump, continuing to react for 22 hours, dropwise adding 11 parts of 35% hydrogen peroxide solution by mass after the reaction is finished, reacting for 50 minutes, cooling to room temperature after the reaction is finished to obtain pale yellow solution, dialyzing, steaming, and freeze-drying to obtain the sulfur quantum dots. (2) Dispersing 8 parts of sulfur quantum dots in 45 parts of deionized water to obtain sulfur quantum dot mixed solution, then carrying out plasma treatment on the sulfur quantum dot mixed solution, adding 2 parts of thioglycollic acid and 0.4 part of 1-hydroxybenzotriazole into the sulfur quantum dot mixed solution after the plasma treatment is finished, stirring and reacting for 3 hours, centrifuging after the reaction is finished, washing and drying to obtain the sulfur quantum dot containing sulfhydryl.
Step S1, adding 24 parts of 4,4 '-stilbene dicarboxylic acid and 14 parts of N-chlorosuccinimide into 45 parts of dichloromethane, stirring for 15min, adding 3 parts of trifluoroacetic acid, stirring and reacting for 20h to obtain a reaction mixture, pouring the reaction mixture into ice water, extracting with ethyl acetate, drying, concentrating, and recrystallizing to obtain chlorinated 4,4' -stilbene dicarboxylic acid;
and S2, adding 7 parts of chlorinated 4,4' -stilbenedicarboxylic acid, 3 parts of 2-fluoro-3-amino-4-methylpyridine, 2 parts of 2-bromo-3-amino-4-methylpyridine and 0.4 part of sulfur containing sulfydryl quantum dot into 65 parts of pyridine, stirring for 50min, adding 15 parts of triphenyl phosphite, heating to 115 ℃, refluxing for 11h, cooling, standing, suction filtering, collecting solid, washing with absolute ethyl alcohol, and drying to obtain the bipyridine bisamide organic ligand capable of regulating the urease activity of soil and inhibiting nitrification.
Comparative example 1
The comparative example provides a preparation method of a bipyridine bisamide organic ligand, which comprises the following steps of adding 8 parts of 4,4' -stilbenedicarboxylic acid and 6 parts of 3-amino-4-methylpyridine into 70 parts of pyridine, stirring for 60min, adding 16 parts of triphenyl phosphite, heating to 120 ℃, refluxing for 10h, cooling, standing, suction filtering, collecting solids, washing with absolute ethyl alcohol, and drying to obtain the bipyridine bisamide organic ligand.
Comparative example 2
This comparative example provides a method for preparing bipyridine bisamide organic ligands, which differs from comparative example 1 in that chlorinated 4,4 '-stilbenedicarboxylic acid is used instead of 4,4' -stilbenedicarboxylic acid.
Comparative example 3
This comparative example provides a method for preparing bipyridine bisamide organic ligand, which is different from comparative example 1 in that 4 parts of 2-fluoro-3-amino-4-methylpyridine and 2 parts of 2-bromo-3-amino-4-methylpyridine are used instead of 6 parts of 3-amino-4-methylpyridine.
Comparative example 4
The comparative example provides a method for preparing bipyridine bisamide organic ligand, and the comparative example is different from comparative example 3 in that the dosage of 2-bromo-3-amino-4-methylpyridine is changed from 2 parts to 1 part.
Comparative example 5
The comparative example provides a preparation method of bipyridine bisamide organic ligand, and the comparative example is different from comparative example 3 in that the dosage of 2-fluoro-3-amino-4-methylpyridine is changed from 4 parts to 1 part, and the dosage of 2-bromo-3-amino-4-methylpyridine is changed from 2 parts to 4 parts.
Comparative example 6
The comparative example provides a preparation method of bipyridine bisamide organic ligand, and the difference between the comparative example and comparative example 1 is that 0.5 part of sulfur quantum dot containing sulfhydryl is added.
Comparative example 7
This comparative example provides a method for preparing bipyridine bisamide organic ligand, which is different from comparative example 6 in that sulfur powder II (average particle diameter is 45 μm) is used to replace sulfur powder I (average particle diameter is 0.5 μm) to prepare sulfur quantum dot containing sulfhydryl.
Performance testing
The bipyridine bisamide organic ligands prepared in the above examples and comparative examples were tested by referring to the requirements of sodium phenolate-sodium hypochlorite colorimetric method for determination of soil urease activity of TNAIA-2020, and by using phenol disulfonic acid colorimetric method for determination of soil nitrate reductase. The test results are shown in Table 1.
TABLE 1 Performance test results
As shown by the performance test results, the comprehensive performance of the bipyridine bisamide organic ligand of the embodiment 1-3 is most outstanding, the soil urease is 156.97-158.82 IU/g, and the soil nitrate reductase is 2.66-2.78 IU/g, mainly because chlorinated 4,4' -stilbene dicarboxylic acid and halogen-containing pyridine compounds are used, and the mercapto sulfur-containing quantum dots are introduced, so that the activity of the soil urease is improved, and meanwhile, the soil nitrate reductase is effectively reduced.
In contrast, comparative example 1, which was significantly inferior to example in terms of the corresponding performance test because the necessary technical scheme was not adopted, resulted in a decrease in the soil nitrate reductase of 134.06 IU/g and a soil nitrate reductase of 4.23: 4.23 IU/g, in contrast to comparative example 1, in contrast to comparative example 2, in which chlorinated 4,4 '-stilbene dicarboxylic acid was used instead of 4,4' -stilbene dicarboxylic acid, the soil urease was increased, in contrast to comparative example 1, in contrast to comparative example 3, in which 4 parts of 2-fluoro-3-amino-4-methylpyridine and 2 parts of 2-bromo-3-amino-4-methylpyridine were used instead of 6 parts of 3-amino-4-methylpyridine, the soil nitrate reductase was decreased, in contrast to comparative example 3, in contrast to comparative example 4, the amount of 2-bromo-3-amino-4-methylpyridine was changed from 2 parts to 1 part, i.e., the mass ratio of 2-fluoro-3-amino-4-methylpyridine to 2, in contrast to comparative example 3, in contrast to comparative example 4, in contrast to comparative example 1, in contrast to 2-fluoro-3-amino-4-methylpyridine was changed from 2 parts to 2 parts, in contrast to 2-fluoro-3-amino-4-methylpyridine was increased from 2-fluoro-3-methyl pyridine, namely, the mass ratio of 2-fluoro-3-amino-4-methylpyridine to 2-bromo-3-amino-4-methylpyridine is less than 1, and the effect of compounding is poor due to the too small amount of 2-fluoro-3-amino-4-methylpyridine, so that the soil nitrate reductase is increased, compared with comparative example 1, the soil urease is increased by adding 0.5 parts of sulfur quantum dots containing mercapto groups to comparative example 6, and compared with comparative example 6, the sulfur quantum dots containing mercapto groups are prepared by using sulfur powder II (particle size of 45 μm, obtained from sigma-aldrich) instead of sulfur powder I (particle size of 0.5 μm, obtained from An Naiji), and the soil urease is reduced due to the poor effect of preparing sulfur quantum dots due to the too large particle size of sulfur powder II. The above experimental results further demonstrate the importance of the technical solutions defined in the present invention to the technical effects thereof.
While the foregoing is directed to the preferred embodiments of the present invention, it will be appreciated by those skilled in the art that various modifications and adaptations can be made without departing from the principles of the present invention, and such modifications and adaptations are intended to be comprehended within the scope of the present invention.
Claims (10)
1. A method for preparing a bipyridine bisamide organic ligand for regulating the activity of soil urease and inhibiting nitrification, which is characterized by comprising the following steps:
step S1, adding 20-25 parts of 4,4 '-stilbene dicarboxylic acid and 12-15 parts of N-chlorosuccinimide into 40-50 parts of dichloromethane, stirring for 10-20 min, adding 2-4 parts of trifluoroacetic acid, stirring and reacting for 12-24 h to obtain a reaction mixture, pouring the reaction mixture into ice water, extracting with an organic solvent, drying, concentrating, and recrystallizing to obtain chlorinated 4,4' -stilbene dicarboxylic acid;
And S2, adding 6-8 parts of the chlorinated 4,4' -stilbenedicarboxylic acid, 4-6 parts of pyridine compound and 0.2-0.5 part of quantum dot material into 60-70 parts of pyridine, stirring for 30-60 min, adding 14-16 parts of triphenyl phosphite, heating to 110-120 ℃, refluxing for 10-12 h, cooling, standing, suction filtering, collecting solids, washing with absolute ethyl alcohol, and drying to obtain the bipyridine bisamide organic ligand for regulating the urease activity of soil and inhibiting nitrification.
2. The method for preparing bipyridine bisamide organic ligand for regulating the activity of soil urease and inhibiting nitrification as claimed in claim 1, wherein the organic solvent in the step S1 is diethyl ether or ethyl acetate.
3. The method for preparing bipyridine bisamide organic ligand for regulating soil urease activity and inhibiting nitrification as claimed in claim 1, wherein the pyridine compound in the step S2 is a halogen-containing pyridine compound.
4. The method for preparing bipyridine bisamide organic ligands for modulating soil urease activity and inhibiting nitrification as claimed in claim 3, wherein the halogen-containing pyridine compound is 2-fluoro-3-amino-4-methylpyridine and 2-bromo-3-amino-4-methylpyridine.
5. The method for preparing a bipyridine bisamide organic ligand capable of regulating the activity of soil urease and inhibiting nitrification as claimed in claim 4, wherein the mass ratio of the 2-fluoro-3-amino-4-methylpyridine to the 2-bromo-3-amino-4-methylpyridine is (1-2): 1.
6. The method for preparing bipyridine bisamide organic ligand for regulating the activity of soil urease and inhibiting nitrification as claimed in claim 1, wherein the quantum dot material in the step S2 is a sulfhydryl-containing sulfur quantum dot.
7. The preparation method of the bipyridine bisamide organic ligand for regulating the activity of soil urease and inhibiting nitrification, which is disclosed by claim 6, is characterized in that the preparation method of the sulfhydryl-containing sulfur quantum dot comprises the steps of dispersing 5-10 parts of sulfur quantum dots in 40-50 parts of deionized water to obtain a sulfur quantum dot mixed solution, carrying out plasma treatment on the sulfur quantum dot mixed solution, adding 1-3 parts of mercaptoacetic acid and 0.2-0.5 part of 1-hydroxybenzotriazole into the sulfur quantum dot mixed solution after the plasma treatment is completed, stirring and reacting for 2-4 hours, centrifuging after the reaction is completed, washing and drying to obtain the sulfhydryl-containing sulfur quantum dot.
8. The preparation method of the bipyridine bisamide organic ligand for regulating the activity of soil urease and inhibiting nitrification, which is disclosed by claim 7, is characterized in that the preparation method of the sulfur quantum dot comprises the steps of adding 4-6 parts of sodium hydroxide and 3-5 parts of polyethylene glycol into 40-50 parts of deionized water in parts by weight, uniformly stirring, adding 1-2 parts of sulfur powder, stirring for 2-4 hours at 70-75 ℃ to obtain an orange red solution, introducing air into the orange red solution by using a peristaltic pump, continuing to react for 20-24 hours, dropwise adding 10-12 parts of 35% hydrogen peroxide solution by mass concentration after the reaction is finished, reacting for 40-60 minutes, cooling to room temperature to obtain a pale yellow solution, dialyzing, steaming, and freeze-drying to obtain the sulfur quantum dot.
9. The method for preparing bipyridine bisamide organic ligand capable of regulating urease activity and inhibiting nitrification as claimed in claim 8, wherein the average particle size of the sulfur powder is 0.5 μm.
10. A bipyridine bisamide organic ligand capable of regulating soil urease activity and inhibiting nitrification, characterized in that the bipyridine bisamide organic ligand is prepared by the preparation method according to any one of claims 1 to 9.
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| US20230339826A1 (en) * | 2020-06-16 | 2023-10-26 | Verdesian Life Sciences U.S., Llc | Formulation system for compositions for enhancing nitrogen stabilizers |
| CN119331280A (en) * | 2024-12-20 | 2025-01-21 | 河北泰能鸿森医疗科技有限公司 | A disposable nitrile wear-resistant glove and its preparation process |
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| US4517003A (en) * | 1983-06-08 | 1985-05-14 | Allied Corporation | N-acyl phosphoric triamide urease inhibitors and urease inhibited urea based fertilizer compositions |
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| CN111484004A (en) * | 2019-01-25 | 2020-08-04 | Tcl集团股份有限公司 | Preparation method of graphene quantum dots |
| US20230339826A1 (en) * | 2020-06-16 | 2023-10-26 | Verdesian Life Sciences U.S., Llc | Formulation system for compositions for enhancing nitrogen stabilizers |
| CN116813923A (en) * | 2023-06-02 | 2023-09-29 | 沈阳化工大学 | A preparation method for fertilizer CuII coordination polymer urease inhibitor |
| CN119331280A (en) * | 2024-12-20 | 2025-01-21 | 河北泰能鸿森医疗科技有限公司 | A disposable nitrile wear-resistant glove and its preparation process |
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